Enterprise Sales & Revenue LeaderApplied AI Systems BuilderAI GTM, Adoption & Agentic Workflows.
Enterprise sales and revenue leader who turns complex technology into revenue, adoption, and measurable business outcomes. Leads strategic selling, rebuilds revenue engines, and connects executive deal strategy with the operating cadence, coaching, and technical fluency required to make growth repeatable.
- 3 fleets
- Agentic AI systems running in production today
- 8 builds
- Shipped and live — every one is below, ask the AI
- $10M → $100M
- ARR scaled — the enterprise GTM career behind the systems
His AI — ask it anything
An AI trained on his full career — wins, numbers, and honest gaps.
It is instructed to tell you when he is the wrong hire. Conversations are logged.
Builds
Shipped, not slideware.
Every build below is real. Ask the AI about any of them — it knows the architecture and the war stories.
Ollie
Agentic OS — a fleet of AI operating systems in production
Ollie started as the operating system that runs JNOW day-to-day and grew into a provisionable fleet: a control plane that stands up complete agentic boxes — agents, dashboards, per-instance auth, and governance — on bare cloud servers. Three instances run in production today. Specialist agents on the Claude Agent SDK share a versioned business brain; a Fleet control plane handles provisioning, updates, role-based access, and health checks; every run is owned, gated, and audited.
- Fleet control plane provisions complete agentic boxes on bare cloud servers — three in production
- Specialist agents on the Claude Agent SDK with a shared, versioned business knowledge base
- Role-based access, human-in-the-loop approval queues, and per-run ownership (the AI Governance layer)
- Voice receptionist tier (ElevenLabs + Twilio) booking appointments end-to-end
- Full memory, usage, and cost telemetry per instance — not a wrapper, the actual control plane behind every JNOW engagement
AI Governance
The policy, approval, and audit layer for autonomous agents
The answer to "how do you let agents act without losing control?" Governance built as a first-class system, not a checkbox: role-based access that fails closed, human approval gates on consequential actions, per-run ownership persisted to Postgres, and full audit trails across a fleet of autonomous agents. It surfaces inside Ollie as a display layer, but the concept stands alone — it came from operating real agent fleets for real businesses, not from a policy deck.
- Fail-closed RBAC — an unknown owner is denied, never assumed
- Human-in-the-loop approval queues for consequential agent actions
- Per-run ownership and audit trail persisted to Postgres — survives restarts
- Exposure health checks and guardrail visibility per user tier
- Proven across three production instances before it had a name
5-Minute Audit Agent
Two-Model Conversational Assessment Agent
AI assessment tool live on jnow.io that asks six questions and returns a custom readout — including an honest take on whether JNOW is the right firm. Two-model architecture: Sonnet handles the conversational turns, Opus generates the final readout. Built in one week and now JNOW's primary client intake mechanism.
- Two-model architecture — Sonnet for conversation, Opus for synthesis
- Session state in Cloudflare KV with 30-minute TTL, hard 12-turn cap
- Voice-eval'd against 20 fictional scenarios before launch
- Cost: ~$0.07 per completed session
- Built in 1 week — JNOW's primary client intake mechanism
AI Resume
The Site You're Looking At Right Now
An AI-queryable portfolio that lets hiring managers ask Claude anything about my background — including the uncomfortable questions most candidates dodge. Built with an "honest AI" philosophy: the system is explicitly instructed to surface weaknesses and poor fits, not just sell.
- Conversational AI powered by Claude — trained on my full career context including private reflections
- Job description analyzer that gives a structured fit verdict with gaps and transferable skills
- Chat-first redesign: the hero IS the conversation — the site demos the skill it claims
- Technical skills section auto-derived from actual project repositories
GetBilled
AI Sales Tools + Full GTM Build for SAP Billing Intelligence
Built the AI-powered sales tooling and the entire go-to-market motion for an SAP-certified billing intelligence platform. The AI components are the load-bearing parts: an account scorer that prioritizes outbound by billing complexity and SAP fit, a Trapped Cash Estimator that quantifies leakage from billing delays, and a value-report PDF generator that auto-produces prospect-specific business cases. The GTM playbook (ICP, messaging, sales process, comp model) is what the AI tools sit inside.
- AI account scorer prioritizing outbound by billing complexity and SAP fit
- Trapped Cash Estimator — interactive ROI calculator embedded in discovery calls
- Auto-generated value-report PDFs with prospect-specific projections
- Outbound automation pipeline connecting intent signals to sequenced outreach
- Full GTM playbook: ICP definition, messaging framework, sales process, comp model
InspectionLens
AI Document Processing for Real Estate Inspections
Turns raw home inspection reports into structured, negotiation-ready summaries. Buyers and agents upload a PDF; the system extracts every issue, categorizes severity, estimates repair costs, and generates a clean summary they can share with sellers. Same architecture pattern applies to legal, insurance, and compliance document workflows.
- PDF parsing and extraction from any inspection report format
- AI categorization by severity: safety hazards, major repairs, cosmetic issues
- Cost estimate ranges based on issue type and regional construction data
- Generates a branded summary document ready for negotiation
- Pattern portable to legal, insurance, and compliance document workflows
FieldKit
Multi-Tenant Field Service Management Platform
Full-stack platform for field service businesses — replacing the spreadsheets and phone calls that most small operators still use. Built for technicians in the field and dispatchers in the office. Multi-tenant architecture with row-level security so each org's data is fully isolated.
- Job dispatch, scheduling, and real-time technician status tracking
- Customer communication portal with automated appointment reminders
- Multi-tenant architecture with row-level security — each org's data fully isolated
- Integrated communications (Twilio, Stripe, QuickBooks)
- Mobile-first UI with optimistic updates for fast performance on spotty connections
IdeaCatcher
Voice-First Idea Capture App (iOS + Android)
End-to-end mobile app built and submitted to both the App Store and Google Play. Captures ideas with voice, text, or camera — then uses AI to tag, organize, and surface related ideas before they get lost. Sub-500ms voice transcription via Deepgram, Claude API for semantic tagging, offline-first architecture with cloud sync.
- Real-time voice transcription via Deepgram with <500ms latency
- Claude API integration for semantic tagging and idea relationship mapping
- Offline-first architecture with Supabase sync when connection restores
- Built for iOS and Android — pending app store approval
Track Record
The receipts.
The career behind the builds. Every role is queryable — the AI knows the real story behind the bullet points.
First GTM & Sales Lead
eSource Solutions
- Own the revenue infrastructure for GetBilled, including ICP definition, category creation, outbound strategy, content architecture, sales enablement, and the Trapped Cash Assessment conversion motion.
- Apply enterprise sales discipline, value-based selling, and pipeline governance to a zero-to-one SAP-certified solution focused on pre-invoice working-capital leakage.
GTM Advisor & Fractional Revenue Leader
Freelance | Self-Employed
- Advised growth-stage companies on GTM diagnostics, revenue architecture, fractional leadership, and applied AI strategy.
- Audited structures, metrics, incentives, and handoffs to identify pipeline friction and improve accountability across Sales, Marketing, RevOps, and Customer Success.
VP of Global Sales
Conversica
- Drove 34% YoY ARR growth through coverage-model redesign, pipeline governance, and a unified operating cadence with Demand Generation and RevOps.
- Closed the largest deal in company history, a $1.5M enterprise license agreement, through cross-functional deal strategy and executive alignment.
- Raised quota attainment from 22% to 105% through execution rigor, coaching, and pipeline governance.
Sr. Director Sales, Midmarket and Enterprise
Conversica
- Increased ASP 36% and reduced sales-cycle time 18% through MEDDPICC discipline, ROI-led selling, and structured deal inspection.
- Delivered a 22% lift in net revenue retention through an expansion strategy built jointly with Customer Success.
VP of Sales, Strategic Accounts
Acoustic
- Increased renewals to 90%, reached 85% expansion attainment, and delivered $4M in new-logo ARR during the post-IBM transition.
- Reset the GTM operating model across compensation, pipeline definitions, qualification criteria, field processes, and the Customer Success-aligned upsell motion.
Worldwide Sales Leader - Watson Marketing Software
IBM
- Owned an $80M global quota and grew market share 25% YoY by aligning sales, demand generation, and product around shared enterprise GTM objectives.
Director of Sales, Retail MidMarket, North America
NetSuite
- Led a $25M P&L, delivered 30% YoY growth, and managed 20 account executives through 3 sales managers.
- Built the retail vertical GTM strategy with field-marketing resources embedded in the sales team.
Earlier IBM Sales & Business Leadership
IBM
- Held worldwide, business-unit, industry, and Tivoli sales leadership roles spanning procurement, commerce, supply chain, marketing, retail, and enterprise systems management.
Thoughts
How I think about GTM, AI, and the intersection of the two
Demand Gen Should Report to Revenue Leadership
Most B2B orgs still silo demand gen under marketing. I think that's broken. When pipeline generation reports to the same leader accountable for closing, you eliminate the handoff friction that kills conversion rates.
Read moreAI Won't Replace Sellers — But It Will Replace Sales Orgs That Don't Use It
The threat isn't that AI replaces your AEs. It's that a competitor with half the headcount and twice the tooling outpaces you. I'm building the tools I wish I had when I was running a 40-person sales floor.
Read moreWhy I Built an AI Resume That Tells the Truth About My Weaknesses
Every candidate site is a highlight reel. I wanted mine to answer hard questions honestly — including "where would you struggle?" and "why did you leave?" If a hiring manager is going to find out, I'd rather they find out from me.
Read moreThe Next Generation of Revenue Leaders Will Write Code
I spent 20 years in revenue leadership before picking up TypeScript. Now I can't imagine going back. When you can build the tools your team needs instead of waiting on a product roadmap, everything moves faster.
Read more